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About Mrs. Betty's Recipe Box

Pineapple Upside Down Cake

Ask me my favorite dessert, and I will always tell you Blackberry Cobbler. Ask me my second favorite, and it’s Pineapple Upside Down Cake.  I’ve had Pineapple Upside Down Cake all sorts of ways, but this one is, hands down, the best I’ve ever eaten! 

This cake is made with crushed pineapple and chopped cherries, instead of just pineapple slices with a cherry in the middle. You get a mouthful of pineapple and cherries in every bite of this cake, but what really makes it stand out from the rest is that wonderful Rum Glaze!

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Holiday Pineapple Down Cake FinishedPineapple Upside Down Cakes became popular in America in the 1920’s after canned pineapple, boxed cake mixes, and electric ovens became accessible. Inverted cakes with fruit were not uncommon, but were typically made on the stove top in a cast iron skillet with other fruits, such as apples and prunes. 

The cast iron skillet was perfect for an inverted cake, since it would caramelize the sugar without burning the butter. I make Mrs. Betty’s cake in my 10-inch Lodge Cast Iron Skillet, and it comes out great. Some things just don’t need changing.

Iron SkilletThis recipe was from a newspaper clipping, and has yellowed more than any other recipe in Mrs. Betty’s Recipe Box. I’m guessing it’s most likely from the 1960’s or 70's. It must have been published around Christmas, since it has ‘Holiday’ in the original title.

Old RecipeIf you want to impress your family or friends this Christmas, put this cake on the dessert table. It won’t last long. Save yourself a piece for the next day, because that's when it's really the best and so moist!

Slice of cakeThe recipe calls for a No. 2 can of crushed pineapple which was about 2-1/2 cups back when cans were numbered by their sizes. A 15.25 can ounce works fine. 

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Start by melting 2 tablespoons butter in a 10-inch cast iron skillet while the oven is preheating to 350 degrees. 

Collage with ornament
Once the butter is melted, add 1/4 cup of brown sugar and mix together. Drain and reserve the juice from the can of crushed pineapple, and mix with chopped maraschino cherries. Spread over the brown sugar and butter mixture in the skillet. 

Mrs. Betty's recipe calls for white cake mix, but my favorite way to make this cake is to use Duncan Hines Signature Pineapple Cake Mix, adding in vanilla instant pudding mix and substituting the reserved pineapple juice in place of water.  

Follow the directions for whichever type of cake mix you are using and pour the batter over the fruit mixture. Bake at 350 degrees for 40-50 minutes. Allow to cool for about 5 minutes, then invert onto plate and give it about a minute or so to plop out of the skillet--that's slang, meaning "to separate beautifully." 

 Inverted skillet

Go ahead and start making the rum glaze while the cake is still in the oven, because you'll want the cake warm when you glaze it. Mix together 1/2 cup sugar, 2 tablespoons butter, 3 tablespoons molasses, 2 tablespoons apple jelly, and 2 tablespoons water.

Don't worry, we'll get to the rum in a bit.

Using a candy thermometer, cook over medium heat, stirring often, until it reaches softball stage, or about 240 degrees.

Rum GlazeRemove from heat, allow to cool slightly, and then stir in a teaspoon of natural rum extract.

A few notes on using rum extract:

Both imitation and natural (or "pure") extracts are made with real rum and contain a higher percentage of alcohol than a rum flavoring. The extract allows you to add the flavor without having to add extra liquid that could upset your baking recipes. Pure rum extract is thicker and creamier than the imitation versions and has a richer rum flavor, such as Cook's Choice Pure Rum Extract, formulated using Myers's Dark Rum. 

Recipe Bottom

After stirring in the rum extract, pour glaze over warm cake.

Enjoy and Merry Christmas!



2 Tablespoons butter

1/4 cup brown sugar, firmly packed

1 (15.25 ounces) can crushed pineapple, drained

6-8 maraschino cherries, chopped

1 package white cake mix (yellow or Duncan Hines Signature Pineapple Cake Mix can be substituted for white cake mix)

Rum Glaze

1/2 cup granulated sugar

2 Tablespoons butter

3 Tablespoons molasses

2 Tablespoons apple jelly

2 Tablespoons water

1 teaspoon rum extract

Preheat oven to 350 degrees. Melt butter in a cast iron skillet.  Remove from heat and add brown sugar; mix well.  Combine pineapple and cherries and spread evenly over sugar mixture.  Prepare cake mix according to package directions. Pour batter over fruit mixture in pan.  Bake at 375 degrees for 40 minutes, or until done.  Remove from oven and allow to stand for 5 minutes.  Invert cake pan onto serving plate and allow to stand 1 minute before removing pan. 

Combine granulated sugar, butter, molasses, jelly, and water.  Cook and stir over medium heat until mixture boils.  Continue cooking, using a candy thermometer, until softball stage (about 240 degrees) is reached.  Remove from heat, cool slightly, and add rum extract.  Pour warm over hot cake, allowing glaze to cover the cake and run down the sides.   

Links to similar Calico Creek pages:

Kid's Birthday Parties and Hosting a Christmas Cookie Exchange

Mrs. Betty's Pecan Divinity and The Peanut Brittle That Built a Church

'Frank Butterscotch' Rice Pudding

Mrs. Betty's Happy New Year Black-Eyed Peas and Tomatoes


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